The main focus of this research program is the development of new methodology for the synthesis of pharmacologically important alkaloids. This chemistry involves investigations into the general reactivity patterns of the five-membered heterocyclic systems, oxazoles. A new synthesis of the antitumor agent ellipticine has been developed by exploiting the Diels-Alder capacity of these heterocycles. In addition, a new strategy for the synthesis of the benzylisoquinoline alkaloids has been achieved. A novel method for the synthesis of substituted oxindoles, and a remarkable reagent for the preparation of active acyl transfer agents have also been discovered. Future work, which relies heavily on the above methodology, will be directed toward the development of an efficient route to the ergot alkaloids (peripheral and cerebral vasodilators).